EP2367532A4 - Method of making small liposomes - Google Patents

Method of making small liposomes

Info

Publication number
EP2367532A4
EP2367532A4 EP09836955A EP09836955A EP2367532A4 EP 2367532 A4 EP2367532 A4 EP 2367532A4 EP 09836955 A EP09836955 A EP 09836955A EP 09836955 A EP09836955 A EP 09836955A EP 2367532 A4 EP2367532 A4 EP 2367532A4
Authority
EP
European Patent Office
Prior art keywords
liposomes
making small
stream
cooling
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09836955A
Other languages
German (de)
French (fr)
Other versions
EP2367532A2 (en
Inventor
Robert A Dupuit
William J Reilley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cascadian Therapeutics Inc
Original Assignee
Oncothyreon Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Oncothyreon Inc filed Critical Oncothyreon Inc
Publication of EP2367532A2 publication Critical patent/EP2367532A2/en
Publication of EP2367532A4 publication Critical patent/EP2367532A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/775—Apolipopeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/1703—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • A61K38/1709—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • A61K38/1735—Mucins, e.g. human intestinal mucin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1277—Processes for preparing; Proliposomes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Organic Chemistry (AREA)
  • Mycology (AREA)
  • Dispersion Chemistry (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Toxicology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Preparation (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Liposomes of constrained particle size are prepared by substantially continuously mixing substantially continuously flowing streams of water, and of an organic solvent contain lipid(s) capable of forming liposomes, and cooling the mixture so liposomes form, the ratio of the flow rate of the stream of water to the flow rate of the stream of organic solvent, and the rate of cooling of said mixture, being controlled so as to obtain a preparation of liposomes such that at least about 90% of the liposomes are of a particle size less than about 200 nm.
EP09836955A 2008-12-17 2009-12-17 Method of making small liposomes Withdrawn EP2367532A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13835308P 2008-12-17 2008-12-17
PCT/US2009/068499 WO2010078045A2 (en) 2008-12-17 2009-12-17 Method of making small liposomes

Publications (2)

Publication Number Publication Date
EP2367532A2 EP2367532A2 (en) 2011-09-28
EP2367532A4 true EP2367532A4 (en) 2012-12-12

Family

ID=42310550

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09836955A Withdrawn EP2367532A4 (en) 2008-12-17 2009-12-17 Method of making small liposomes

Country Status (12)

Country Link
US (3) US20120034294A1 (en)
EP (1) EP2367532A4 (en)
JP (2) JP2012512260A (en)
KR (1) KR101452033B1 (en)
CN (2) CN102256595A (en)
AU (1) AU2009333177B2 (en)
BR (1) BRPI0923001A2 (en)
CA (1) CA2747182C (en)
EA (1) EA020604B1 (en)
MX (1) MX2011006562A (en)
SG (1) SG172257A1 (en)
WO (1) WO2010078045A2 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201204410A (en) * 2004-04-01 2012-02-01 Oncothyreon Inc Mucinous glycoprotein (MUC-1) vaccine
JP5771366B2 (en) * 2009-09-02 2015-08-26 株式会社バイオメッドコア Liposome production apparatus and method
WO2012116225A2 (en) 2011-02-24 2012-08-30 Oncothyreon Inc. Muc1 based glycolipopeptide vaccine with adjuvant
KR101387575B1 (en) * 2012-08-10 2014-04-23 서울대학교산학협력단 Liposome having acetylene moiety and phospholipid and use thereof
US9693958B2 (en) * 2013-03-15 2017-07-04 Cureport, Inc. Methods and devices for preparation of lipid nanoparticles
CN107427791B (en) * 2015-03-19 2021-05-14 康涅狄格大学 System and method for continuous manufacture of liposomal pharmaceutical formulations
TWI774752B (en) * 2017-04-13 2022-08-21 國立大學法人北海道大學 Flow channel structure and method for forming lipid particles into micelles using the same
SG11202110036RA (en) 2019-03-19 2021-10-28 Arcturus Therapeutics Inc Method of making lipid-encapsulated rna nanoparticles
EP3711749A1 (en) * 2019-03-19 2020-09-23 Polymun Scientific Immunbiologische Forschung GmbH Method of making lipid nanoparticles
WO2023041588A1 (en) 2021-09-14 2023-03-23 Advapharm Gmbh Novel lipopeptide formulation

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005373A1 (en) * 1999-07-15 2001-01-25 Inex Pharmaceuticals Corp. Methods and apparatus for preparation of lipid vesicles
US20030235610A1 (en) * 2002-06-21 2003-12-25 Piedmont Pharmaceuticals, Llc Liposomes containing biologically active compounds
WO2004071638A2 (en) * 2003-02-11 2004-08-26 Regents Of The University Of California, The Microfluidic devices and method for controlled viscous shearing and formation of amphiphilic vesicles
US20050112184A1 (en) * 2003-11-26 2005-05-26 Andreas Jahn Controlled vesicle self-assembly in continuous two phase flow microfluidic channels
WO2005112546A2 (en) * 2004-04-01 2005-12-01 Biomira, Inc. Mucinous glycoprotein (muc-1) vaccine
US20070264320A1 (en) * 2006-05-09 2007-11-15 The Regents Of The University Of California Microfluidic device for forming monodisperse lipoplexes

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11139961A (en) * 1997-11-06 1999-05-25 Taisho Pharmaceut Co Ltd Production of liposome
EP1045688A1 (en) * 1998-01-16 2000-10-25 Biomira Usa Inc. Lipomatrix preparation
WO2001036433A2 (en) * 1999-11-15 2001-05-25 Biomira, Inc. Synthetic lipid-a analogs and uses thereof
DE60134265D1 (en) * 2000-12-01 2008-07-10 Biomira Inc PREPARATION OF LIPOSOME BY INFUSION IN PEG
EP1855669A4 (en) * 2005-01-28 2010-07-07 Bc Cancer Agency Liposomal compositions for parenteral delivery of agents
TWI511738B (en) * 2005-06-28 2015-12-11 Oncothyreon Inc Method of treating patients with a mucinous glycoprotein (muc-1) vaccine
CN103989633A (en) * 2005-07-27 2014-08-20 普洛体维生物治疗公司 Systems and methods for manufacturing liposomes
US20080089927A1 (en) * 2006-04-06 2008-04-17 Vladimir Malinin Methods for Coacervation Induced Liposomal Encapsulation and Formulations Thereof
JP5126874B2 (en) * 2007-05-21 2013-01-23 国立大学法人神戸大学 Method for producing liposome preparation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005373A1 (en) * 1999-07-15 2001-01-25 Inex Pharmaceuticals Corp. Methods and apparatus for preparation of lipid vesicles
US20030235610A1 (en) * 2002-06-21 2003-12-25 Piedmont Pharmaceuticals, Llc Liposomes containing biologically active compounds
WO2004071638A2 (en) * 2003-02-11 2004-08-26 Regents Of The University Of California, The Microfluidic devices and method for controlled viscous shearing and formation of amphiphilic vesicles
US20050112184A1 (en) * 2003-11-26 2005-05-26 Andreas Jahn Controlled vesicle self-assembly in continuous two phase flow microfluidic channels
WO2005112546A2 (en) * 2004-04-01 2005-12-01 Biomira, Inc. Mucinous glycoprotein (muc-1) vaccine
US20070264320A1 (en) * 2006-05-09 2007-11-15 The Regents Of The University Of California Microfluidic device for forming monodisperse lipoplexes

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
ANDREAS JAHN ET AL: "Controlled Vesicle Self-Assembly in Microfluidic Channels with Hydrodynamic Focusing", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 126, no. 9, 1 March 2004 (2004-03-01), pages 2674 - 2675, XP055036501, ISSN: 0002-7863, DOI: 10.1021/ja0318030 *
ANDREAS JAHN ET AL: "Microfluidic Directed Formation of Liposomes of Controlled Size", LANGMUIR, vol. 23, no. 11, 1 May 2007 (2007-05-01), pages 6289 - 6293, XP055036503, ISSN: 0743-7463, DOI: 10.1021/la070051a *
ANDREAS JAHN ET AL: "Preparation of nanoparticles by continuous-flow microfluidics", JOURNAL OF NANOPARTICLE RESEARCH ; AN INTERDISCIPLINARY FORUM FOR NANOSCALE SCIENCE AND TECHNOLOGY, KLUWER ACADEMIC PUBLISHERS, DO, vol. 10, no. 6, 15 February 2008 (2008-02-15), pages 925 - 934, XP019612177, ISSN: 1572-896X *
ANONYMOUS: "Cancer Vaccines, New Research", 2006, NOVA SCIENCE PUBLISHERS, INC., XP002686068 *
ANONYMOUS: "Medical applications of liposomes", 1998, ELSEVIER SCIENCE B.V., XP002686069 *
PRASHANT PRADHAN: "A Facile Microfluidic Method for Production of Liposomes", ANTICANCER RESEARCH, March 2008 (2008-03-01), pages 943 - 948, XP055036500, Retrieved from the Internet <URL:http://ar.iiarjournals.org/content/28/2A/943.full.pdf#page=1&view=FitH> [retrieved on 20120827] *
S. BATZRI ET AL: "Interaction of phospholipid vesicles with cells. Endocytosis and fusion as alternate mechanisms for the uptake of lipid-soluble and water-soluble molecules", THE JOURNAL OF CELL BIOLOGY, vol. 66, no. 3, 1 September 1975 (1975-09-01), pages 621 - 634, XP055189859, ISSN: 0021-9525, DOI: 10.1083/jcb.66.3.621 *

Also Published As

Publication number Publication date
JP5895030B2 (en) 2016-03-30
KR101452033B1 (en) 2014-10-21
WO2010078045A3 (en) 2010-10-28
CN102256595A (en) 2011-11-23
SG172257A1 (en) 2011-07-28
AU2009333177A1 (en) 2011-07-07
AU2009333177B2 (en) 2013-09-19
US20120034294A1 (en) 2012-02-09
JP2012512260A (en) 2012-05-31
JP2014224127A (en) 2014-12-04
MX2011006562A (en) 2011-09-27
EA020604B1 (en) 2014-12-30
WO2010078045A2 (en) 2010-07-08
EP2367532A2 (en) 2011-09-28
US20130330398A1 (en) 2013-12-12
CA2747182C (en) 2014-11-18
EA201100829A1 (en) 2012-02-28
US20150315217A1 (en) 2015-11-05
CA2747182A1 (en) 2010-07-08
BRPI0923001A2 (en) 2018-09-18
CN105935352A (en) 2016-09-14
KR20110094114A (en) 2011-08-19

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Effective date: 20121114

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Ipc: C07K 14/775 20060101ALI20121106BHEP

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Effective date: 20140709

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